103

Chestertown, MD Homes for Sale

Section Image
  • 0 Lenapah Rd, Chestertown, MD 21620
    0 Lenapah Rd, Chestertown, MD 21620
    /2

    $10,000

    • Land
    • 0.34 Acre
    • $29,412 per Acre

    0 Lenapah Rd, Chestertown, MD 21620

    Discover your own piece of paradise in Lenapah, Chestertown, MD! This expansive 14,500 square foot lot offers endless possibilities for your dream home or investment vision. Nestled in a serene setting, this raw land is ready for your creative touch. Embrace the tranquility of nature while being just a short drive from local amenities. Whether you’re looking to build your dream oasis or a savvy

    Solomon Zaldivar Compass

    0 Lenapah Rd, Chestertown, MD 21620
  • 0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620
    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620
    /2

    $59,000

    • Land
    • 1.37 Acres
    • $43,066 per Acre

    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620

    (Lot 2 - .685 acres & Lot 3 - .689 acres) Conveniently located slightly off 291, in a private area on a dead-end road, this property is close to Chestertown and minutes away from route 301. Lots sit high off the road level and adorned with young saplings. Soil evaluation from 2011 approved for 3 beds and a 2,000 sq ft home, located just outside the critical area. Lots being sold together!

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620
  • 0 Elm Rd, Chestertown, MD 21620
    0 Elm Rd, Chestertown, MD 21620
    /2

    $40,000

    • Land
    • 0.33 Acre
    • $121,212 per Acre

    0 Elm Rd, Chestertown, MD 21620

    Water oriented community of Tolchester Estates. Public record says Montgomery but the correct address is Elm Road. Approved for sewer allocation. Please see recent survey in documents.

    Vaughn Hogans The Hogans Agency

    0 Elm Rd, Chestertown, MD 21620
  • 127 Wood Duck Ln, Chestertown, MD 21620
    127 Wood Duck Ln, Chestertown, MD 21620
    127 Wood Duck Ln, Chestertown, MD 21620
    /26

    $215,000

    • 3 Beds
    • 2 Baths
    • 1,666 Sq Ft

    127 Wood Duck Ln, Chestertown, MD 21620

    Tom Riccio RE/MAX Point Realty

    127 Wood Duck Ln, Chestertown, MD 21620
  • 0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
    /8

    $150,000

    • Land
    • 2 Acres
    • $75,000 per Acre

    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620

    Sebrin Adem RE/MAX Allegiance

    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
  • 0 Montgomery Unit MDKE2003418, Chestertown, MD 21620
    0 Montgomery Unit MDKE2003418, Chestertown, MD 21620
    /2

    $40,000

    • Land
    • 0.11 Acre
    • $363,636 per Acre

    0 Montgomery Unit MDKE2003418, Chestertown, MD 21620

    Vaughn Hogans The Hogans Agency

    0 Montgomery Unit MDKE2003418, Chestertown, MD 21620
  • 0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620
    0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620
    /2

    $28,000

    • Land
    • 2 Acres
    • $14,000 per Acre

    0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620
  • 0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620
    0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620
    /2

    $38,000

    • Land
    • 0.34 Acre
    • $111,765 per Acre

    0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620
  • 23710 L Rd, Chestertown, MD 21620
    23710 L Rd, Chestertown, MD 21620
    /2

    $24,000

    • Land
    • 0.5 Acre
    • $48,000 per Acre

    23710 L Rd, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    23710 L Rd, Chestertown, MD 21620
  • 0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620
    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620
    /2

    $37,000

    • Land
    • 0.34 Acre
    • $108,824 per Acre

    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620
  • 0 Spinnaker Rd, Chestertown, MD 21620
    0 Spinnaker Rd, Chestertown, MD 21620
    /2

    $38,000

    • Land
    • 0.56 Acre
    • $67,857 per Acre

    0 Spinnaker Rd, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Spinnaker Rd, Chestertown, MD 21620
  • 0 Rd, Chestertown, MD 21620
    0 Rd, Chestertown, MD 21620
    /2

    $120,000

    • Land
    • 1.8 Acres
    • $66,667 per Acre

    0 Rd, Chestertown, MD 21620

    Live just down the road from Fairlee Creek! Public access is less than a mile away allowing the Chesapeake Bay at your fingertips! Great Oak Marina sits at the inlet of Fairlee Creek and The Bay offering a full service resturant, marina and Tiki Beach Bar. A summer full of entertainment, boating, fishing, crabbing, jet skiing, tubing, skiing or anything else your heart deserves! Public water and

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    0 Rd, Chestertown, MD 21620
  • 0 Buck Neck Landing Rd, Chestertown, MD 21620
    0 Buck Neck Landing Rd, Chestertown, MD 21620
    /2

    $9,500

    • Land
    • 0.34 Acre
    • $27,941 per Acre

    0 Buck Neck Landing Rd, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Buck Neck Landing Rd, Chestertown, MD 21620
  • 103 Metcalf Rd, Chestertown, MD 21620
    103 Metcalf Rd, Chestertown, MD 21620
    103 Metcalf Rd, Chestertown, MD 21620
    /25

    $259,900 New Construction

    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    103 Metcalf Rd, Chestertown, MD 21620

    Brand new home in Historic Chestertown available for move-in this October. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you’ll find generously sized bedrooms including a large primary suite with

    David Moore Real Broker, LLC

    103 Metcalf Rd, Chestertown, MD 21620
  • 492 Pear Tree Point Rd, Chestertown, MD 21620
    492 Pear Tree Point Rd, Chestertown, MD 21620
    492 Pear Tree Point Rd, Chestertown, MD 21620
    /11

    $920,000 Open Sat 10AM - 2PM

    • 3 Beds
    • 2 Baths
    • 2,632 Sq Ft

    492 Pear Tree Point Rd, Chestertown, MD 21620

    Welcome to 492 Pear Tree Point Road: an exceptional Chester River waterfront home with unique upriver views. Spacious rooms, gorgeous hardwoods, a back deck to die for, private setting, and with space to add; this home has it all! Good water depth for a dock and center console. Nearly an acre of elevated land - out of the flood zone - that backs to picturesque horse pasture. The main floor

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    492 Pear Tree Point Rd, Chestertown, MD 21620
  • 0 Fairlee-Melitota Rd Unit MDKE2005726, Chestertown, MD 21620
    0 Fairlee-Melitota Rd Unit MDKE2005726, Chestertown, MD 21620
    0 Fairlee-Melitota Rd Unit MDKE2005726, Chestertown, MD 21620
    /4

    $50,000 Coming Soon

    • Land
    • 0.5 Acre
    • $100,000 per Acre

    0 Fairlee-Melitota Rd Unit MDKE2005726, Chestertown, MD 21620

    The building lot you’ve been waiting for!Half-acre, mostly cleared, and wonderfully private, tucked down a quiet gravel road with few neighbors. A survey has been ordered and the county confirms a water/sewer allocation is available for $16,200 at buyer's expense. Conveniently located just outside the small town of Fairlee and close to Chestertown, Rock Hall, and multiple boat ramps for all

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Fairlee-Melitota Rd Unit MDKE2005726, Chestertown, MD 21620
  • 124 Char Nor Manor Blvd, Chestertown, MD 21620
    124 Char Nor Manor Blvd, Chestertown, MD 21620
    124 Char Nor Manor Blvd, Chestertown, MD 21620
    /5

    $245,000 Open Sat 10AM - 12PM

    • 2 Beds
    • 2 Baths
    • 1,024 Sq Ft

    124 Char Nor Manor Blvd, Chestertown, MD 21620

    Welcome to 124 Char Nor Manor Blvd, a charming home tucked away on a quiet street in Chestertown. This residence offers the perfect balance of comfort, convenience, and lifestyle, all within the highly sought-after Queen Anne’s County school district.Step inside to find a warm and inviting space with high ceilings and skylights flooded with tons of natural lighting. Continue into the living

    Crystal Smith RE/MAX Executive

    124 Char Nor Manor Blvd, Chestertown, MD 21620
  • 126 Char Nor Manor Blvd, Chestertown, MD 21620
    126 Char Nor Manor Blvd, Chestertown, MD 21620
    126 Char Nor Manor Blvd, Chestertown, MD 21620
    /4

    $349,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,304 Sq Ft

    126 Char Nor Manor Blvd, Chestertown, MD 21620

    *Please join us for our Open House Saturday, September 20th from 1:30pm-3:30pm*This charming 3 bedroom, 2 bathroom home offers the perfect blend of comfort, convenience, and functionality that has major upgrades including Fresh Paint throughout, Renovated Primary Bath and New carpet. The bonus office room is an essential for remote work! The property also features a large 2-car

    Crystal Smith RE/MAX Executive

    126 Char Nor Manor Blvd, Chestertown, MD 21620
  • 109 2nd St, Chestertown, MD 21620
    109 2nd St, Chestertown, MD 21620
    109 2nd St, Chestertown, MD 21620
    /9

    $15,000

    • Land
    • 1.8 Acres
    • $8,333 per Acre

    109 2nd St, Chestertown, MD 21620

    ONLINE AUCTION: Bidding begins 10/15/2025 @ 10:00 AM. Bidding ends 10/17/2025 @ 12:40 PM. List Price is Suggested Opening Bid. Deposit: $5,000+/- 1.80 AC lot in Chestertown (Kent County). Existing structure is uninhabitable; offered as land only. Short distance to the Chester River with convenient access to nearby marinas, parks, and in-town amenities. Buyer to verify utilities, access,

    Adam Shpritz Ashland Auction Group LLC

    109 2nd St, Chestertown, MD 21620
  • 0 Beltram Rd, Chestertown, MD 21620
    0 Beltram Rd, Chestertown, MD 21620
    0 Beltram Rd, Chestertown, MD 21620
    /6

    $10,000

    • Land
    • 0.34 Acre
    • $29,412 per Acre

    0 Beltram Rd, Chestertown, MD 21620

    POST AUCTION! Make an offer, buy it now! 2 Lots available for sale as package in Kent County, MD. on Fish Hatchery Rd, Bunting Rd, Beltram Rd, and Towhee Rd. Call for details. Lot of Land located in Chestertown, Maryland within Kent County. Property is in close proximity to Worton Creek Marina, and all the attractions in Chestertown, Maryland. Property is Vacant. Easy Access to Major

    Adam Shpritz Ashland Auction Group LLC

    0 Beltram Rd, Chestertown, MD 21620
  • 0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620
    0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620
    0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620
    /7

    $10,000

    • Land
    • 0.37 Acre
    • $27,027 per Acre

    0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620

    POST AUCTION - Make an offer, buy it now! 2 Lots available for sale as package in Kent County, MD. on Fish Hatchery Rd, Bunting Rd, Beltram Rd, and Towhee Rd. Call for details. Lot of Land located in Chestertown, Maryland within Kent County. Property is in close proximity to all the attractions in Chestertown, Maryland. Property is Vacant. Easy Access to Major Traffic Artery Chestertown

    Adam Shpritz Ashland Auction Group LLC

    0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620
  • 0 Texas Ave, Chestertown, MD 21620
    0 Texas Ave, Chestertown, MD 21620
    /2

    $10,000

    • Land
    • 0.09 Acre
    • $111,111 per Acre

    0 Texas Ave, Chestertown, MD 21620

    POST AUCTION: MAKE AN OFFER! Lot of land in Tolchester Beach, Maryland located within Kent County. Nearby attractions include Tolchester Marina and +/- 7 miles to all the attractions in Rock Hall, Maryland. Easy Access to Major Traffic Artery Rock Hall Road. Deposit: $5,000.

    Adam Shpritz Ashland Auction Group LLC

    0 Texas Ave, Chestertown, MD 21620
  • Parcel Buck Neck Ldg Rd, Chestertown, MD 21620
    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620
    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620
    /6

    $10,000

    • Land
    • 0.34 Acre
    • $29,412 per Acre

    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620

    POST AUCTION: MAKE AN OFFER! Lot of Land located outside of Chestertown, Maryland within Kent County. Nearby attractions include Warton Creek Marina, Warton Creek, Attractions along Chesapeake Bay, & +/- 7 Miles to downtown Chestertown, Maryland. Easy Access to Major Traffic Artery Fairlee Road. Deposit: $5,000.

    Adam Shpritz Ashland Auction Group LLC

    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620

Showing Results 81 - 103, Page 3 of 3

Maryland Kent County Chestertown

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